Pharmaceutical product



Patented Mar. 20, 1928.

ETED STATES PATENT OFFICE- WALTER SCHOELLER, ADOLF FEIiDT, MAX GEHRKE, AND ERICH BORGWARDT, OF BERLIN, GERMANY, ASSIGNORS TO FIRM: CHEMISCHE FABRIK AU]? ACTIEN, (VORM. ,E. SCHERING), OF BERLIN, GERMANY PHARMACEUTICAL PRODUCT.

No Drawing. Original application filed May 9; 1925, Serial No. 29,207, and in Germany June 2, 1924.

' Dividedand this application filed June 1, 1926. Serial No. 113,07'3.

Our invention refers to pharmaceutical products and more especially to products obtained from amino metal mercapto benzene compoundsyit further refers to the methods 5 of making such products. The new products are distinguished from the amino metal mercapto benzene compounds by a greater stability of the watery solutions of'their salts and by a more favorable chemo-therapeuti- 10 cal coefficient. We obtain. them by causing phosgene or a phosgene substitute to act on the compounds mentioned above in the form of their acids or salts. I

We thus obtain products in which two equal benzene amino radicals are connected by the acyl of carbon dioxide to form a symmetrical urea, compound according to the formula 10 NH Ar G00.Y S Me The new products are preferably used in the form of their soluble salts, more especially sodium salts, by subcutaneous or ntravenous injection.-

In producing the new compounds accordmg to the present invention we preferably proceedas follows:v Example 1. Phosgene is introduced under stirring into a 10 per cent solution of grams of the sodium salt of the 4-amino-2- .argento mercapto benzene-l-carboxylic acid until no further diazo reaction occurs; the reaction nnxture is kept slightly alkaline. The precipitate is separated by filtration,

rinsed, dissolved in soda solution and the sodium salt of the diphenyl urea compound COONa COONa @Szig OSAR NH o0 NH COONa GOONa @Sriu 08A:

NH-CO-NH is thus obtained in quantitative yield as a solid body of yellowish green color readily dissolving in alkalis and ammonia. The solutions thus obtained are absolutely stable; they can be heated to boiling for a long period without showing any signs of decomposition. The product obtained is separated by filtration, is well rinsed with water, dissolved in caustic soda solution and precipitated with alcohol.

We wish to to be understood that we do not desire to be limited to the exact substances, proportions, conditions and sequence aene-para-carboxylic acid) urea, correspondmg to the formula COO-Na S.Au

of operations above described for obvious modifications will occur to a person skilled in the art.

In the appended claims the term acid is designed to include also the soluble salts of the respective acids.

lVe claim 1. As a new product, the derivative of an amino metal mercapto benzene compound corresponding to the formula ar coo y S-Me wherein Ar is a benzene nucleus, Me is a heavy metal, Y 1s hydrogen or a metal,

i more especially an alkali metal, such product as an acid dissolving only With difficulty, as an alkali salt readily in water and having'a therapeutical effect more especially in cases caused by spirochaetae.

2. As a new product the sodium salt of the symmetric di- (meta-auro-mercapto ben- S.Au

capto benzene-l-carboxylic acid with phos gene.

In testimony whereof we afiix our signatures.

WALTER SCHOELLER, ADOLF FELDT. MAX GEHRKE. ERICH BORGWARDT. 

